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Chemistry of Heterocyclic Compounds

, Volume 23, Issue 6, pp 614–624 | Cite as

Structures and photo- and thermochromic properties of spiropyrans of the 2-oxaindan series with polycondensed chromene fragments

  • S. M. Aldoshin
  • V. A. Lokshin
  • A. N. Rezonov
  • N. V. Volbushko
  • N. E. Shelepin
  • M. I. Knyazhanskii
  • L. O. Atovmyan
  • V. I. Minkin
Article

Abstract

Spiropyrans of the 2-oxaindan series with 2H-chromene fragments benzo- and 2,3-naphthoannelated at the 7–8 bond were synthesized. The molecular structures of four of the spiropyrans obtained were determined by x-ray diffraction studies, and their photo- and thermochromic properties were studied. Annelation of arene rings significantly increases the relative stabilities fo the photocolored forms of the spiropyrans. A correlation between the length of the Cspiro-O bond and the capacity of spiropyrans for photocoloration was discovered. In addition, the free energies of activation of the thermochromic transformations of spiropyrans determined by dynamic NMR spectroscopy are insensitive to variations in the length of the indicated bond.

Keywords

Spectroscopy Chromene Free Energy Organic Chemistry Molecular Structure 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1987

Authors and Affiliations

  • S. M. Aldoshin
    • 1
  • V. A. Lokshin
    • 1
  • A. N. Rezonov
    • 1
  • N. V. Volbushko
    • 1
  • N. E. Shelepin
    • 1
  • M. I. Knyazhanskii
    • 1
  • L. O. Atovmyan
    • 1
  • V. I. Minkin
    • 1
  1. 1.Scientific-Research Institute of Physical and Organic ChemistryM. A. Suslov Rostov State UniversityRostov-on-Don

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